440 problems/quenching?/advice needed

I'm sure you've noticed not one person is laughing or ridiculing you. If it were mine and I were trying to work on a tight budget I'd start by changing the cam. There are so many good hydraulic cams to choose from and most are reasonably priced. Some of the other guys have mentioned the intake fitment with milled heads and decked block. I agree, you may also have a mis-match between the intake and heads. Since you will need to remove the intake to swap the cam and lifters anyways it gives you a chance to check that out. When the heads sit lower because of milling them and decking the block it requires the intake to be more narrow to fit. One tell-tale sign the intake is too wide is trouble getting the intake bolts in. if you look into the intake bolt holes and they appear to be higher than the bolt holes in the heads than the intake is too wide. If so you either need to get the intake milled or the the intake mounting surface of the heads milled. The general rule is the intake gets milled 123% of what was milled off the heads on the combustion chamber side. I.E. if the heads were milled .050" you would mill .062" off the intake mounting surfaces. With all that said once you get the cam swapped do a cranking cylinder pressure test to see where you're at. With iron heads you should be OK for pump gas up to around 150-160 psi. Remember when doing this test you either do it with no carb on or have the throttle wide open when you're doing it. If the cranking pressure is too high then you will need to go to larger chamber heads. Once you get all that sorted out its a matter of tuning and a decent 440 will give you plenty of power for cruising and burning rubber, you're going to love it.